Potassium Carbonate → HCID 18924378, compound

HRID 1288635Notes

Reaction equation

HRID 1288635 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18][N:17]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:16][CH2:15][N:14]([C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:43](=[O:46])([O-])[O-].[K+].[K+]>C(#N)C>[CH3:9][O:8][CH2:1][CH:2]([N:20]1[CH2:19][CH2:18][N:17]([C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[CH2:16][CH2:15][N:14]([C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:22][CH2:21]1)[CH2:3][O:46][CH3:43]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 151342581,4,7-Tris-(benzyloxycarbonyl)-1,4,7,10-tetrazacyclododecane

Product 1

HCID 18924378HCID 18924378, compoundYield 400%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

39 g (154.6 mmol) of the title compound of Example 5a and 44.43 g (77.3 mmol) of 1,4,7-tris-(benzyloxycarbonyl)-1,4,7,10-tetraazacyclododecane (produced according to Chem. Soc., Perkin Trans. 1, 12:3329, 1991) and 85.14 g (616 mmol) of potassium carbonate in 800 ml acetonitrile are refluxed for 24 hours. Solid is filtered out, and the filtrate is evaporated to dryness in a vacuum. The residue is taken up in 700 ml of methylene chloride and extracted twice with 300 ml of water. The organic phase is dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel (mobile solvent =methylene chloride/methanol 20:1).

Sources & evidence

ORD record
ord-eb2cc69e86c84f49867500be9e602217
Source dataset
uspto-grants-1998_05
Patent number
US05747000

Reaction notes

Loading…